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Construction of the 4-Azafluorenone Core in a Single Operation and Synthesis of Onychine.

Victoria A LehmanYun MaJonathan R Scheerer
Published in: The Journal of organic chemistry (2024)
This study describes the synthesis of the 4-azafluorenone core in a single operation using readily available starting materials. Condensation of an amidrazone with ninhydrin intercepts an intermediate 1,2,4-triazine derivative, which engages norbornadiene in a merged [4 + 2]/bis-retro[4 + 2] sequence to deliver the azafluorenone core. The tricyclic core established in this manner was elaborated to onychine, the simplest natural product in the 4-azafluorenone alkaloid family.
Keyphrases
  • ionic liquid
  • high resolution
  • amino acid